Dear Rob,
I’m in a slightly unfamiliar situation. Maybe, out of the kindness of your seemingly bored, stranger-helping heart, you could give me some advice.

First off, after reading several of your past entries/responses (which I enjoyed quite immensely, by the way), I am already anticipating your advice, which will most likely be to drop any further attempts at some sort of relationship-like bond with this guy beyond simple (ha!) platonic friendship. So I implore you also to give me an alternate set of advice in which I do pursue such… relations.

All pointless information aside, I am a 16 year old girl (for accuracy’s sake, I’m 17 in a month) who is well, having problems with a guy.

Oh god, the dreaded clichés have already come for me. Do overlook that too, hmm?

I really don’t want this to become a long-winded description/explanation, but there are several factors that can’t be ignored. My apologies in advance. Still, I’m pretty sure I’m going to end up typing the collective life story of me and my love interest.

I’ll start at the beginning. (Or vice versa, if you wish.)
A short while ago, I self-diagnosed myself with want-what-I-can’t-have-itis (thrill of the chase, fear of even the slightest bit of commitment, those lovely little bad habit truisms). All too common, I know, but I decided to get rid of it since I already had enough problems as it were. At the same time, I was a typical female who “liked” anything that was attractive enough by my standards and had a pulse.
Ah yes, the good ol’ days. After getting more or less cured, I did realize that I actually do look for specific things in a guy, that I don’t want a relationship with just any gorgeous, animate objects, etc. And I’m through with the bad, dangerous type. They’re so boring. This is where Paul comes in.
Paul is quite remarkable. Suffice it to say that he truly has what I am looking for. I had been attracted to him in the past, but this was also during my streak with bad boys…sheesh. Oh and there was also the fear of commitment, i.e., dating or the likes.

Although a great deal of recent encounters, flirting, body language, and exchanges between us are, in my mind, extremely pertinent to the situation, I’ll omit them for brief descriptions of the most key events.

Like most guys, from my understanding, he is painfully vague when talking to me about certain… situations or problems. Unlike most guys, it seems he is attempting to drop hints in these exchanges and skillfully using elaborate analogies in doing so.
It is my belief that on the last day of school, after the yearbooks had been signed and almost everyone had gone, he intended to ask me out, but chickened out, so to speak. What I extracted from his analogy (which he gave me later that day on IM) was that he was all set on asking me out, but his ride took the opportunity from him. The analogy essentially makes perfect sense if I input the situation of him wanting to ask me out, but for all I know that’s not what he’s trying to say. He said he really should have stayed after longer, and, as the analogy goes, “given the closing, and pissed off my carpool.” (i.e., asked me out in whatever brilliant fashion he was set on, and pissed off his carpool.)

So basically, the situation that I’m in right now is that after not going online for at least a year, the guy I like suddenly gets a screen name on the evening of the last day of school, tracks my screen name down on yahoo, and cryptically tells me that he should have stayed later that day to tell someone (I know that it’s a female), something “courageous” and perfectly planned out that would have prompted some sort of judgment from this girl, and that he regrets not doing. For the record, I was the only girl there during the time he was talking about, save for a few irrelevant freshman girls.
After that, we’ve been talking every night for a few hours on IM (I even got him to stay an hour longer one night – quite a feat considering he lives in a “police state”) until a few days ago, as he is now in California visiting prospective colleges. From what I have gathered… he has a case of wanting what he can’t have. It’s rather complicatedly tied in with his personal beliefs, and he isn’t too keen on getting out of it. He’s said that he’s “picky,” and also that he (paraphrased) wishes that he wouldn’t chicken out so much. I’m quite sure that he can’t decide if he wants to have a relationship or not.

Yet at the same time, he drops hints of really wanting one; this among countless other things – one of my guy friends actually proposed to me the other day (we’re really close, and he wasn’t completely serious), and I told Paul that, asking him what I should tactfully say in return. Upon telling him my guy friend had proposed to me, he said “sneaky bastard, beat me to the punch…” Also things like only talking to me on IM, and pissing off a few of his friends in the process.

A few days before he left for California, I asked him if he could possibly come over to play a video game that we had been planning on playing together (although the initial plan was to do so over the internet, which I realized won’t work. Yes, we’re both total nerds). He said sure, after the time he’d be gone. He also said that he’d try to keep in touch over that time, but he most likely wouldn’t be able to (he hasn’t so far). The problem is…I feel I’ve been a bit over eager – quite a rarity for me. I even gave him my email address, and told him to use it if he felt the need (nothing yet). That, along with asking him to come over, something the likes of which I had unsuccessfully nudged at in the past, and more makes me feel like I’m being much too keen.

I can’t be so overtly eager or I’ll scare him off. At the same time, I can’t play too hard to get and flirt with other guys because I’m afraid he’ll think I’m uninterested, and he’ll think I wasn’t really being serious with him (from personal experience, this seems like a possibility). What can I do to attain this precious balance yet have the relationship actually progress, to see if he really wants to be with me, and to find all this out without coming off like some deranged, needy chick?
Thanks for any help
– Sue

Hi Sue,
I feel for you, I really do.
When a guy is getting all the signals to ask a girl for the date and he wimps out, it’s very frustrating.
For the both of you.

Here’s an analogy for you:
He’s the batter at the plate.
The bases are loaded. No outs.
The pitcher (you) are giving him all the signals that your pitch is going to be a soft lob ball, right over the plate. Easily hit out of the park.
And what does are batter do?
He passes and let’s another batter take his place.
He’s so scared of failure, or rejection, so lacking in self-confidence that even when given the green light (literally flashing before his eyes), when he has the perfect opportunity to be the hero, he walks away.
Then, after the game he talks with the pitcher and says stuff like:
“I had that one but my arm was stiffening up”
“I could’ve cleared the bases but I had a cramp in my leg”
And other crappy statements that infer he could have been the hero but the time just wasn’t right.

So, how do you handle this type of guy?
You have to step up and complete the deal.
The next time you see him, in person, after chatting a bit and catching up you say to him, quite plainly, “Are you going to take me on a date or what?” Then give him a kiss.
Seal the deal for him.
And yes, likely you’ll be adopting a puppy-man. Willing to sit, stay and roll over on your request.
He will be all mushy, dependant on you, constantly jealous and always needing to know where you are.
But, in the end, you’ll have received your request.
You will be dating this puppy-man.

So there you are, how to date the man that shows all the signals that he wants to date you but he just can’t bring himself to ask the question.
End his pain. Make the completion.
Ask him the question.Best Wishes,
Rob.